Benzoxazolone arsonic compounds



Patented Nov. 8, 1927..

UNITED STATES PATENT OFFICE.

srenon no I. G. GERMANY.

FARBENINDUSTRIE AKTIENGESELLSGHAFT, A CORPORATION OF BEN ZOXAZOLON'EKRSONIC COMPOUNDS.

No Drawing. Application filed ,afune 2, 1924, Serial No. 717,439, and in Germany June 9. 1923.

, My invention relates to a new benz-oxazolone arsomc compound of the formula:

which may be obtained either by acting with phosgene on the corresponding 'ortho-amino-" The new compound represents a yolk-coloured powder insoluble in water, onlysparingly soluble in dilute caustic soda solution, it dissolves in a hydrochloric acid suspension with the addition of sodiumnitrite.

This-solution is colorless and cannot be coupled with the azo components, whilst the primary material under identical conditions -yields a yellow diazo compound which changes to an intense red if coupled with resorcine. 2.

100 gr 4-amino-3-hydroxybenzene-1-arsonic'acid are dissolved at 7080 C. in 1200 cc. sodiumacetate solution double normal.

Into the solution which has "been cooled down to ordinary temperature phosgene is introduced until the solution shows a strong mineral acid reaction. The product of re- 'on I v +2 coon-4 no1+ tiondiseases. In contrast to its parent-materlals it possesses 'a lesser toxicity and better stability.

50 gr. -4.4 -diamino-3.3 -dihydroxyarsenobenzene-hydrochloride (Benda B344, p. 3 579/1911) are dissolved-with the exclu- S1011 of airin 2000cc. water and 2300-00. caustic soda solution 10 times normal.

Phosgene is introduced at ordinary temperature.- If an acid reaction .has set in, fur ther 200 cc. caustic soda solution are added 10 times normal and this proceeding repeated until a test cannot be diazotized'any longer. The precipitate is filtered by suction,well washed with water,- alcohol and ether in a current of nitrogen, and dried in vacuo.

The aforesaid reaction takes ing to the following equation:

NHO-0 Nn'o-o place accordhydrochloric acid,then' is added at ordinary temperature a solution prepared as follows 100 gr. sodium hypophosphite are dissolved in,50 cc. of hot water and mixed with 200 and 500- cc. methylated spirit; the cooled ing to the following equation: NH--o=o NiI-o-o NHVO=O place accordred.

AaOaE cc. hydrochloric acid 1.18 specific gravity Having now particularly described and ascertained the nature of my said invention and in what manner the same is to be performed, I declare, that what I claim is:

5 As a new product the benzoxazolone arsonic compound of the formula:

which is when dry a yolk-colored powder,

dilute caustic soda solution, soluble in a hydrochloric acid suspension with the addition ofsodium nitrite to a colorless solution, which cannot be coupled with azo components, said compound being substantially identical with sucha one obtainable by acting with pliosgene on'4.4-diamino 3.3-dihydroxy-benzene-1-arsenobenzene or by treating the 4-amino-3-hydroxy-benzene-l-arsonic acid with phosgene and reducing the benzoxazolone'arsonic acid thus formed to the arsenocompound.

' In witness whereof I have hereunto signed my name this 16th day of May, 1924.

LUDWIG BENDA. 

